Earlier this year, I was sitting in this outstanding modern Italian restaurant – literally next door to the celebrated David Burke Townhouse (for the foodies among you) – and indulging in one of the best pizzas I’ve had in a long time. Actor Ricky Gervais strolled past me on his way to the table overlooking 61st Street. All the diners stare – some text friends. Fame by proximity; so very New York.

That Mr. Gervais is decked out in nylon running pants, sneakers, a random jacket and an old – or perhaps “vintage” – tee shirt is apropos given that my dining companion was bespoke clothier Jon Green.

Jon is a remarkable guy, both in personality and skill. Within a certain circle, he is very much a celebrity in his own right – but he’s not a tailor. He’s a clothier; a distinction he is always quick to make. Publicly, Jon is perhaps best known for being profiled by Forbes magazine after once crafting a $25,000 suit. “Not a particularly practical suit,” he told me. “The fabric was very expensive and no really conducive to daily use.”

Perceived reputation notwithstanding, Jon is actually a very practical and modest man. Though always impeccably turned out, he owns only a handful of his own make of suits, along with a few blazers. A multitude of shirts and selection of neckwear round out his work wardrobe.

Should I even have to mention that, with a starting price of around $9,000, no, I do not yet count a Jon Green bespoke suit among my own wardrobe’s holdings?

The level of hand detail in a Jon Green suit is astonishing.

We chatted about a number of things, from his philosophy on dressing well to the possible development of a new, lower-priced line. All things being relevant, “lower-priced” in this case means in the range of $5,000.00. He’s a voraciously intellectual guy who is fascinated with everything, not a bad trait when your customers literally include global captains of industry. He also a counselor and guide, confidant and referee. Above all he a perfectionist, exactly the trait needed in this highly discerning field.

Jon is a bespoke designer, and that in and of itself is a very specific designation. The word “bespoke” is derived from the English verb of the 17th century to bespeak, “to speak for something, to give order for it to be made.”

The standards of Bespoke clothing requires the creation of a paper pattern, hand cutting of the cloth with shears, and the highest level and amount of hand, needle, and iron work by a master coat maker, pant maker, and waistcoat maker. In fact, the cloth used in bespoke is often itself, bespoke. Jon told me about once traveling to a mill in England to monitor the manufacture of a specific order.

Both made-to-measure and ready-to-wear garments are cut from a ready-to-wear block pattern, with or without alterations, and constructed and finished in the same way as ready-to-wear in a factory.

Jon, in his Madison Avenue studio

The bespoke suit is the gold standard of male dress and the suit to which every other aspires. The process of crafting a Jon Green bespoke suit starts with taking the measure, rather than the measurements, of the man.

It begins with a conversation about the person – his sartorial likes and dislikes, his personal style. Within the broad traditions of classic tailoring, one can define their own look. Jon’s goal is not just to create a garment that fits perfectly, but to create a garment that perfectly fits his client.

The ultimate goal, as with other craftsman of his caliber, is to create a lifelong learning experience where the client at first relies on Jon, but comes to trust their own taste the more they learn about what styles suit them best.

Jon is also occasionally asked to provide his sartorial insights to a broader audience – like the discerning readers of Departures magazine.

So, what was Jon wearing at our dinner? Jeans, navy cashmere turtleneck and a 15-year old blue blazer of his own make – recently re-lined.

A few years ago, I wrote about achieving what I broadly referred to as the “college professor” look. Grounded more in cherished stereotype than classroom fact, the tweeds, corduroy, tortoise shell glasses and leather dispatch case round out an idealized look.

While more inspiration than practical, this style embodies classic Ivy League charm and blends well with the current brainy/East Coast preppy trend.

Having so dispensed with the hypothetical, I felt suitably up to the challenge when one of my closest friends, a high school teacher, asked me to write a column on how he could upgrade his professorial wardrobe. The real deal, as it were.

His everyday wardrobe is fairly casual; khakis, jeans, polo shirts and sweaters are staples. Though he’s never been a suit and tie kind of guy, Bob (not his real name of course) now wants to dress in a more professional manner. He runs a major department at his school, which also means a fair amount of public exposure, and wants a wardrobe to reflect this level of responsibility.

He wants to project authority and professionalism without looking overdone, and in this case a daily coat and tie would be overdone. He’s not a banker, he’s a teacher; but does not mean he isn’t a professional. Bob is very good at what he does and wants his appearance to project that ability and experience.

What is needed here is an in-between look; professional but not stuffy, relaxed but still grown up. One of the quickest ways to do this is by focusing on fit and tailoring. You don’t have to give up your personal style to pull on a more polished look because you’re not changing who you are. But you do need to pay attention to how you translate your personal tastes into a more refined style.

In Bob’s case, as with many guys stuck in a dressing-for-college-class mindset, that means making a few key changes. Often, the simplest things make the biggest impact. Ditch shapeless worn out khakis in favor of tailored pants and swap baggy, faded jeans for fitted dark washed ones instead. Rather than rely on sweatshirts, try pima cotton crew neck or v-neck sweaters. It’s all about reinterpreting your outdated college-era wardrobe for the grown up you.

For many men, navigating the waters of business wardrobes without the benefit of a business suit can be a little scary. Suits are easy and authoritative. But for someone in Bob’s situation, a suit makes no sense.

In his case, odd jackets and blazers are the best solution. An odd jacket, be it corduroy, tweed, flannel or cotton, will provide the formality and authority of a suit coat but do in a comfortable and relaxed fashion.

Odd jackets can also be paired with almost any kind of outfit and give it a polished, finished look. And these days a jacket does not automatically necessitate a tie. I love ties, I personally think they are a wonderful way to express personality. But achieving a complete outfit sans tie is easily done with this kind of dressing. Layer a fine gauge sweater over a patterned shirt, or added a pocket square. These approaches can provide needed texture, color and detail.

Paying attention to fit and detail can lead to innovative discoveries.

Bonobos, for example, makes truly innovative khakis. Not your plain old wardrobe staple, Bonobos pants are contoured and cut to actually fit a body and fit it well. They have legitimately changed the playing field when it comes to casual pants. With a uniquely shaped waist line that wraps around your midsection in a way that eliminates so-called “diaper butt,” where the seat of your khakis bunches up, creating an unflattering silhouette.

A simple strait leg and lightly updated classic designs help Bonobos become the best option for a casually professional pant. The brand is also moving into jackets, shirts and partnering with other equally innovative brands.

Yes, it does mean investing in a new type of wardrobe, and some of that investing can be pricey – especially if Bob expands his shopping horizons and comes to appreciate the outstanding fit and quality of, say, a Brioni sport coat.

Frankly though, that is not the ultimate goal. You do not need to idealize famous clothing brands in an effort to dress well and project a stylish, confident – and confidence inspiring, for that matter – look.

The real point is that Bob will now be buying clothes that can last for life and can be added to over time. He is creating a new kind of wardrobe that can grow and evolve as he and his career grow and evolve. The fact that he wants to do all this is the most important thing of all. We are judged by how we look and how we carry ourselves. These days, now more so than ever, you are in charge of your career and you are your best marketing consultant.

I think it’s safe to say that for generations now, polo shirts have been the cornerstone of a classic warm weather wardrobe. Though when they hear polo shirt most people think “Polo ™” shirt, the first truly branded version was developed in 1929 for tennis legend Rene’ “The Alligator” Lacoste.

Lacoste wanted a comfortable shirt to replace the traditional, but totally impractical dress shirt and tie worn by tennis players at the time. In doing so, he unwittingly produced one of the most versatile garments ever conceived.

With its unique ability to straddle the elusive line between casual and formal, the classic polo can carry you from the office to the country club with little difficulty. While I do not suggest that a knit polo shirt is right for every occasion, when paired with a sharp outfit you should be covered for pretty much anything short of a State Dinner.

The corporate casual lookPairing a polo shirt with khakis is the traditional choice and usually works just fine for most situations. This looks works equally well with either a worn-in, laid back outfit or your pressed and crisp, off-to-cocktails-on-the-lawn togs.

And unless you are a 15 year-old prep school miscreant, take pass on the overly stylized graphic, patched and logoed polos – they are just not meant for grown-ups. Same goes for the excessively “vintage aged” khakis. When going “nice” casual, keep the overall feel less stuffy with clean boat shoes or penny loafers and a woven leather or ribbon belt.

Classic white poloA little logo overkillFor a more business look, try a dressy belt with a silver monogrammed buckle, blue blazer and high grade slip-ins from Alden. I’ve occasionally seen a black polo paired with a pinstriped suit; very sharp in a George Clooney sort of way. If you are going to give that a try, opt for a very fine-gauge shirt in a silky finish.

Whatever look you’re trying to achieve, make sure to follow these simple guidelines to always be your best when sporting a polo shirt this summer. First, as always, ensure that the fit is right.

Avoid going too baggy. A trim fit across the shoulders – so the shirt’s shoulder seams actually land on your shoulder – should be your first goal. You don’t want any pulling or bunching, just a natural and comfortable fit. The body of the shirt should lightly touch yours, but not pull or feel tight.

The sleeve should hit somewhere around your mid-bicep and be fitted but not at all constricting. When un-tucked, your shirt should hang no lower than your hips and by no means cover your rear like some kind of mini skirt.

Regardless of how well it fits, when in the office, keep your shirt tucked in.

Even when you’re going for a younger look, say with modern jeans and some vintage shoes, a trim fit will keep everything looking fresh. Many designers have come out with slimmer fitting polo shirts, so make sure you try on several brands and see what feels best. And trim does not mean tight – unless you want it tight of course, which is another look altogether.

He can pull off a really fitted poloOne of the best things about polo shirts is their versatility. They come in almost any color under the sun, from basic white to jet black, solids or preppy stripes. Polo shirts also happen to age very well.

That beat up old polo at the bottom of the shirt drawer – the one with the seriously frayed collar? It will look great at a clam bake with some faded khaki shorts and a stiff gin & tonic.

To my mind, the cooler months are to men always the kindest when it comes to getting dressed in the morning. That’s when we get to pull out the fun clothes and really take advantage of the many options that make classic menswear great. We get to layer.

I’m talking about stuff like chunky longwings, cords and a well worn jacket, topped it off with a warm cashmere scarf. The sheer variety of cold weather clothing is something many guys look to as the temperature drops.

For those of us with the flexibility to move between business dress and corporate casual, something I call the “Rumpled Look” is a nice middle alternative to being strictly dressed up or dressed down. Originally an offshoot of the American Preppy aesthetic, the rumpled look has come into its own. It’s not an attempt to be sloppy, instead it is an homage to worn in classic comfort.

The basic idea behind this look is the allusion to old money, classic taste, and timeless style. Newer or continental styles don’t lend themselves to celebrating beat up and handed down clothes quite like the preppy culture does. The unspoken message of the slouchy khakis, un-ironed oxford shirt and slightly beat up shoes is that you have old money, an Ivy League education, a summerhouse in the Hamptons, and you sail a lot.

Or at least you dress like you do.

Lapo: Master of the Stylish RumpleThis really is a fun look which is not hard to carry off well as long as you don’t try too hard. It’s sort of the antithesis to the recent “critter” trend, which left every inch of pants, ties, belts and coats adorned with embroidered animals and icons of every sort – from dogs to martini glasses. Instead of sartorially hitting people over the head with your East Coast airs, stick to a less-is-more aesthetic. One creative article of clothing at a time is nicely ironic, more is overkill.

Simple but ClassicFor most men, wearing this look at the office can be a bit tough, but depending on your company’s culture, distressed chinos matched up with an un-ironed button down under a crew neck sweater should be just fine. For a younger look, don’t tuck in the shirt but rather let it hang out under the sweater – just make sure to choose a short bodied shirt. I’ve found that J. Crew button-downs are often just right. Wear a washed tweed jacket over the whole outfit. This kind of layering effect is another signature of the rumpled look.

Additionally, make sure to opt for clothes that actually fit well. The rumpled look is not an excuse to go baggy or oversized, it is more of a toned down and worn-in take on being well dressed.

Uncomplicated but still DetailedOne of the best things about this type of style is that you can effectively mix high and low to meet int he middle. For example, to meet up with friends for drinks, try pairing a permanently wrinkled (read, make a point of not ironing it) Thomas Pink dress shirt with dark but worn-in jeans and a sport coat. The juxtaposition of classic and casual is a key balance to this look.

Like any other style you want to incorporate into your own, stop and look in the mirror before leaving the house. What’s most important is that you are happy with the overall feel and proportion of your outfit. The goal should be to look like you’ve had everything for years and don’t think twice about getting dressed.

Way back in the ‘80s getting dressed for the office, assuming you worked at an office, was fairly easy. It was a suit. Not a good suit mind you, but a suit. Boring shirt, forgettable tie and cap toe shoes.

More often than not the whole outfit was forgettable because so little personality was evident. Even the leading men’s fashion book of the time, the landmark “Dress For Success” essentially encouraged its readers to dress like everyone else, but perhaps in a finer cut of suit.

It was a stifling period of time that helped lend fuel to the dot-com boom of the 1990s which, among other things, turned the world of work clothing on its head. At its apex, the rules that governed the very concept of business attire and professional decorum were being tossed out the window wholesale. In formally formal workplaces casual Fridays were adopted and the predictable erosion of style ensued.

The work world devolved into a sea of pleated khakis and denim shirts.

Fast forward to today. Men’s clothing is back with a vengeance. There are many factors that went into this sea change – much of a backlash against the hyper casual-cum-sloppy look which had become annoyingly prevalent by the early ‘90s. After the economic collapse of 2008, many companies began reinstating some form of dress code and all this coincided with a resurgence of interest in men’s fashion. What’s different now is that personal style is the rule rather than the exception.

THE NEW COOLMen are finally taking back what they gave up decades ago – good taste, style, and a sense of swagger. If the “Decade of Gap” gave us anything sartorially useful, it is the realization that guys do, in fact, have a real desire to feel good about how they look. It also gave the menswear industry the chance to essentially reinvent itself.

Dressing well is the new cool and a key aspect to the new cool is taking classics and reinterpreting them. Designers like Michael Bastian, Zanone (part of Slowear) and Billy Reid are injecting new life and a fresh perspective into classic menswear and making it feel new again.

And it’s definitely not all about suit anymore. In fact, for a lot of men a suit is simply another option in the wardrobe; not a sacred stand-alone piece reserved for special occasions. The middle ground of of dressy casual, or business casual in office speak, is where many guys live Monday through Friday and much of the growth in the menswear market is geared for just that.

Billy Reid’s timeless yet casual look

Some companies like J. Crew are being called out (by some OTC readers to be sure) for overdoing it and making the classics look more like caricature. I don’t disagree that for some brands the “new preppy” is being beaten into formulaic iteration.

But not to worry, dressing well – and on your own terms – is fairly simple if you remember a couple of rules.

DON’T BE A “LOOK”First and foremost, be true to yourself. Know what kinds of clothes you like and what looks good on you. Always pay attention to style, fit, balance and purpose. The clothes you wear should match your style and personality, they need to fit you well, they need to work with each other, and they need to make sense.

A SUIT STILL MAKES ANY GUY LOOK GOODWearing a suit every day makes life relatively easy – just find a shirt and tie that match.

Even if you aren’t leading a board meeting, you can still suit up in a dressed down way. Skip the tie altogether and toss on a patterned shirt with a shorter spread collar and high second button.

President Obama popularized this look on the campaign trail while sporting mainly solid white or blue shirts. George Clooney also makes this work; but then again he’s George Clooney.

Obama’s popular open collar look

Clooney goes for an extra button

The main point is that you don’t want to look like you forgot your tie – you want to look like you don’t need one. To inject a little color into the outfit, pocket squares are a simple option.

When it comes to the suit, classic really is best: single breasted, notch lapel, two-button. If you want to personalize a little bit, try peaked lapels instead of notched and double vents instead of the standard American single vent.

If you really want the three-button jacket go for a “3/2 roll” which just means that the top button rolls with the lapel and gives the overall appearance of a two-button jacket. Try and avoid ventless jackets, they can seem dated and are frankly uncomfortable to wear.

If this is your first “good” suit classic grey or blue will be most versatile. Take some time and pick a shade that best suits your complexion and personality. You can always add patterns and striped later.

Ede and Ravenscroft of London – a very nice suit

Always keep in mind that depending where you are in the country, or world for that matter, regional traditions will always dictate what is appropriate. A sport coat and nice pants may be considered dressy in Las Vegas, but if you’re meeting in New York it should probably be coat and tie.

SANS THE SUITWhile dressing well doesn’t necessarily mean dressing up, that is no excuse to look like you’re taking out the trash.

Even when you’re not obligated to, try and go for a more polished look when heading off to the office. That means tailored clothing – stuff that both fits your style but also your body. Properly fitted clothes makes you look better, thinner and smart. The look below, from Hermes, is an excellent example of a casually stylish outfit that would look great on almost anyone.

Hermes: Fall 2009

A classic blue blazer, with or without brass buttons, is an exceedingly useful article of clothing. It’s the workhorse of your wardrobe and can cover you in most any situation. Pair it with dress pants and a cashmere sweater, beat up khakis and polo shirt, or your favorite jeans and Turnbull & Asser shirt; it works with everything.

Well fitting, classic separates So, don’t be afraid to try something new and bring your work wardrobe into the 21st century. By updating classic cornerstones – the suit, the blazer, the dress shirt and the pocket square – you can give your own sense of style a grown up look without looking dated.